


truth or dare

by jhoom



Series: truth or dare [1]
Category: Supernatural
Genre: Blowjobs, College!AU, Dirty Talk, M/M, Multi, NSFW, PWP, Threesome, Twincest, Underage Drinking, handjobs, roommate!AU
Language: English
Status: Completed
Published: 2016-07-21
Updated: 2016-07-21
Packaged: 2018-07-25 20:34:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,600
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7546653
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: <blockquote class="userstuff">
              <p>Dean gets roped into a game of truth or dare with his roommates Castiel and Jimmy.  The game keeps getting more and more ridiculous, until suddenly Dean finds out something he’s not really sure he was supposed to.</p>
            </blockquote>





	truth or dare

**Author's Note:**

> just to be clear, this is entirely [destielonfire](http://archiveofourown.org/users/kaidanmono/gifts)'s fault
> 
> first of three ??? ish deanjimstiel stories i've apparently decided i *need* to write. don't have a name for the series yet, so there's nothing to subscribe to (boo), but you can always check [my tumblr](http://jhoomwrites.tumblr.com) for updates (yaaay)

Dean stretches out in his desk chair, listening to his joints pop as they finally get to relax a little.  It’s Friday night and here he is, writing a fucking paper.  

Somehow he got it in his head that he’d get a head start on his English essay before the weekend.  And yeah, okay, not like it’s _bad_  to get ahead in his homework, but it’s boring as hell writing about whether or not Hardy really had the whole work planned out or if he changed things midway through as necessary.  Dean’s basically had to read the whole damn book over again, and that’s a pretty shitty way to start the weekend.

The sound of jingling keys outside the door saves him from his writing nightmare.  

"Fucking hell, Benny," Dean grouses when his roommate finally gets the door open.  It's a good hour past when he said he'd show up and they were supposed to hang out.  "I've been going crazy over here!  Tell me you got it."

"Well," Benny drawls out as he pulls off his backpack and starts rummaging through it.  "I've got good news and I've got bad news in that regard."

"Ugggggh."  He throws up his book and slams his head on his desk to emphasize his exasperation.  "You're killing me."  

Benny waits for the theatrics to end before he pulls out a bottle of whiskey.  Walking over, he places it right next to Dean's laptop and smirks smugly.

Dean instantly perks up.  "You got it?  Fuck, man, you made me think your football buddy didn't come through."

"Course he did."  Benny gives him a winning half-smile before he looks away.  "I mentioned there was bad news."  He waits until he has Dean's full attention (which Dean grudgingly gives him only after making a show of looking over the label, opening the bottle and sniffing the whiskey).  "So turns out Andrea asked me out-"

"You're ditching me for a chick?"  Dean apparently oversells his scowl and appalled tone, because Benny actually looks contrite.  He laughs and punches Benny's leg.  "Dude, seriously, I don't care.  I know how badly you've been wanting to go out with her.  Go have fun, stay out late, get into trouble, whatever.  We can drink another time."

"You sure?"  And yeah, he looks so damn hopeful that Dean's a little jealous Benny found a girl that he's _this_  into.  

"Yeah, I'll be fine."   _Bored, but fine._

Benny thanks him about five more times as he changes.  He's about to head back out when he spots Dean looking longingly at the bottle of whiskey, half-hidden behind his desk lamp in case the RA comes by.  

"You don't have to wait for me to drink it.  Consider it a gift."

"I'm not going to drink by myself," he scoffs.  Sure, he'll probably take a sip just to try it, but it's no fun getting buzzed by himself.

"You could ask the twins."  And like that he's gone, leaving Dean to think about that possibility.

It's not exactly an unappealing one.  Jimmy and Castiel are their suite mates.  The two bedrooms are connected by a small bathroom.  They hang out a decent amount - it's impossible to ignore each other when four guys share the same bathroom - but usually at the dining hall or when their dorm holds movie nights.  They're cool guys, so it's not exactly like it'd be putting Dean out to see what they're up to.  

And Dean can think of a million worse ways to spend his Friday than drinking with two ~~hot guys~~  friends.  

Before he can change his mind, he grabs the bottle and heads through the bathroom.  He stops at the door to their room and knocks, because he might be a bit overeager at the idea of having two new drinking buddies but he's not _rude_.  

A pair of blue eyes and messy hair greet him as the door swings open.  Dean hesitates, bites his bottom lip to buy more time, then says, "Heya Cas."

"Hello Dean."  Cas moves aside to let him in, gesturing toward the chair at the foot of his bed.  

He pats Cas on the shoulder as he walks by, throws a wave Jimmy's way, and takes a seat.  He keeps the bottle behind his back for a dramatic reveal.

Castiel and Jimmy are identical twins.  Like, freakishly identical.  There's _nothing_  different about the way they look, down to the way they dress.  Hell, he's pretty sure they share clothes.  It threw Dean for a loop the first few weeks of the semester.  He couldn't tell them apart at _all_ , didn't even realize there were _two_  of them until he happened to see them in line together at the bookstore.  

(And THAT was embarrassing.

"There are _two_  of you."

"Yes."

"Dude, we _live next door_ to you.  How did you not realize that?"

Yeah, they probably think he's a fucking genius.)

( ~~It'd been pretty fucking awesome to find out that the hotness quotient next door had doubled, though.~~ )

Of course, once they started actually spending time together, it became painfully obvious that they're different.  Cas is more quiet and reserved, more thoughtful and maybe a tad aloof.  Jimmy was almost always smiling and joking around, more physical and self-assured.  Dean spent way too much time trying to figure out which one he liked more before realizing he really didn't give a shit.  They're both awesome in their own ways and there's no point in choosing between them.

"Look what Benny gifted us."  He holds up the bottle like it's the holy grail.  And really, considering they're three 19 year olds without a fake ID between them, it so is.  

"Sweet!"  Jimmy practically jumps off his bed and grabs the whiskey right out of Dean's hands.  "This could get us nice and fucked up if we wanted to."  He opens the and makes to take a drink.

"Whoa whoa whoa, hold your horses there."  Dean snatches it back.  Jimmy pouts but doesn't retaliate.  "We gotta lay some ground rules here."  

"Your whiskey, your rules?" Jimmy asks around a too big smile.  

"Something like that."  He holds the bottle just out of Jimmy's reach in case he tries something.  "We need a drinking game to go with our drinking."

Cas frowns at him.  "That seems inefficient."

"Lighten up, Cas.  The point isn't to get drunk-"  Cas gives him a pointed look as Jimmy laughs in disbelief.  "I mean, yeah, it _is_ , but we're not going to just _waste_  it.  This is good stuff."  He takes a sip and winces.  "Okay, well, it's _strong_  stuff.  Gotta savor it."

"What'd you have in mind?"  Jimmy's taking these little half steps forward.  Dean finally gives in and hands it over ( ~~and maybe watches the way his lips curve around the top and his Adam's apple bobs as he swallows~~ ).

"I believe most drinking games require equipment that we don't have," Cas points out.  It's all Dean can do to pull his eyes away from Jimmy and consider what Cas is actually saying.  Noting Dean's confusion, he adds, "We don't have an adequate table for beer ping, nor do we have any cups or ping pong balls.  No cups means no flip cup.  Unless you have a deck of cards, that eliminates several other games-"

"Alright alright, I get it, geez."  And okay, yeah, Cas isn't exactly wrong, but way to burst his bubble.  "When'd you become an expert at drinking games, anyway?  You research them or something?"

The silent way Cas stares back at him suggests that he did in fact research them.   ~~Fuck, that's adorable.~~

Jimmy snaps his fingers.  "Got one.  Nothing needed but some alcohol and creativity."  When neither Dean nor Cas react, Jimmy's shoulders slump.  "Seriously?  No guesses?  C'mon guys, don't make me be the fun one-"

"Jimmy."  It's not loud or particularly forceful, but there's an underlying authority in the way Cas says it that has Jimmy stopping dead in his tracks.  The brothers share a look, some sort of secret twin communication or something, and Dean feels like a third wheel for a second.  

Then Jimmy's back to grinning evilly, a twinkle in his eye as he annouces, "Truth or dare."  

"That's such a kid game," Dean whines in disappointment.

"Children aren't allowed to drink," Cas intones helpfully.  

"Neither are _we_."

"Then perhaps it is a fitting choice in game."  And the fucker has a coy little smile trying to ruin his otherwise stoic face.

Dean opens his mouth to argue some more (not really because he has a problem with the game or is even annoyed with Cas, but there's something fun about seeing how Cas will respond), but Jimmy waves his arms to cut them off.

"Okay okay, stop.  We're playing.  Here's the rules.  All standard truth or dare rules apply.  Drinking additions: you can refuse to answer a question, but you gotta take a shot.  You _cannot_  refuse a dare-"

"Jimmy," Cas warns, and there's a hint of something stronger underneath.  "Remember Meg's party in the seventh grade?"

He flushes immediately and looks uncharacteristically tongue-tied at that.  Seeing an opportunity for what it is, Dean asks, "Oh please do tell, what happened at Meg's party in the seventh grade?"

The brothers stare each other down until Jimmy gives in.  Looking at the ceiling, he chooses his words carefully.  "I may have been dared by our friend Meg to go up to Mrs. Milton and slap her ass.  And Cas may have said it was a bad idea and told me I shouldn't.  And that may have made me want to do it more.  And I may have been banned from ever going to like... half the kids' houses in our neighborhood after that."

Dean's cracking up from 'slap her ass' all the way to the end and needs a full two minutes to recover.  "Oh my _god_ , you're one of _those_."

"He is," Cas says solemnly.  "So I suggest that there be a contingency in place for either refusing or requesting modifications to dares."

"Ugh, fine."  Jimmy's brow wrinkles in concentration.  It's an expression Dean's seen on Cas' face a dozen times, but usually when he doesn't get some reference or when he finds Dean's behavior particularly strange.  Even with his mirror image doing it, Dean's staggered by how different Jimmy looks wearing that frown.  "Okay.  If you flat out refuse a dare, you gotta do three shots.  If you ask for a modification, you only have to do one shot.  Fair?"

Dean nod-shrugs his agreement.  There's a good chance that one of them will dare another to do something _outrageous_  with the hope of forcing them to drink.  Not that Dean really cares, he's game for just about anything (and once the alcohol starts burning its way through his system, he'll be up for even more).  If someone tries to work the system, he's pretty sure he can get it to go in his favor.  "Can we add you get to reward yourself with a shot for every successful dare completed?"

"Obviously."

"I don't understand."  And yeah, there's that little frown back on Cas' face.  On Jimmy it managed to look mischievous, while on Cas it's cute.  Er, _almost_  cute.  If you're into that sort of thing.  Which Dean isn't.  "Is the point to avoid drinking or to encourage it?"

Jimmy laughs and slaps his brother on the back.  "A little bit of both."

By some unspoken agreement, they start with a round of Truth's to test the waters.  Jimmy claims he gets to go first since the game was his idea, and rounds on Dean.  "Dean Winchester.  Truth or dare?"

"Truth."  

"What's the dumbest thing you've ever done?"

"Uh," he scrambles for an answer.  There's plenty of dumb things for him to choose from, but none of them are all that interesting or story-worthy.  There was the time he _almost_  snuck out and took his dad's car for a joyride, but he'd chickened out at the last minute.  With nothing else, he "The redhead at the mixer a few weeks back?"

Jimmy's laughter rings out (and hey, look at that, he even got a small smile out of Cas).  "Not where I was going with that question, but I'll take it.  Your turn."  

"Cas, truth or dare?"

They get through a whole round without anyone opting out of answering.  The questions are kinda personal, but not super invasive so there's no point.  Which is fun in the 'getting to know my roommates better' sense, but terrible for the 'aren't we supposed to be drinking?' aspect.

"Castiel."  Jimmy sings the name, elongating each syllable a beat longer than necessary.  "Fuck, marry, kill: me, Dean here, and Benny."

Dean nearly chokes on his non-existent drink.  Does he want to know the answer to this?  Does he _really_  need to know if Cas would want to fuck him?  No, he does not need that kind of temptation.  That'd make things awkward, right?  So, bad idea.

Fuck that, he wants to know.  Needs to know if he has a shot with _either_  twin.  How long would be too long to wait before making a move if Cas is interested-?

Cas wordlessly motions for the bottle and takes a long swig.  

Well that's... really fucking disappointing.  Goddammit, he got his hopes up.  

He nearly misses Cas turning on him and asking, "Truth or dare?"

"Truth."  Then under his breath, he adds, "Man, I feel like you're targeting me."  Jimmy's last turn is in fact the only exception, both twins routinely hounding Dean.

"Everyone keeps picking truth.  I already know everything about Jimmy, so there's no need to ask."

"Okay, new rule!  You can't pick the same thing two times in a row, or else you gotta drink."  Jimmy looks so damn proud of himself.  Dean does admit it's probably a good addition.  "This is in fact a retro-active rule update, so that's one shot for me, two for Cas, and four for you Dean?"  

Cas looks like he's about to intervene on his behalf, but Dean reaches for the whiskey and takes a long long drink, more than encompassing the four shots he's been assigned.  He winks at Jimmy when he's done and passes him the bottle.

"Dean."  And there is _no way_  Cas should sound that serious about friggin' truth or dare.  And really, it's unfair that his voice is getting rougher with the alcohol.  (Because it's either Cas' voice or the liquor he drank that are doing... _things_  to him.  How's he supposed to focus on playing when he's trying not to pop a boner?)  "Describe the last porn video you watched."

He's not sure if his face is bright red or completely white, but his head is fuzzy and his tongue sits limply in his mouth.  The last porno he watched?  Well, fuck... there'd been two guys, both with messy dark hair, going at it pretty damn hard.  They were fighting to pin down the other, as if the winner would get to fuck into the other guy.  Which is exactly what happened.  One of them managed to use his belt to tie down the other one, held him down with one arm and his body while he used his free hand to open him up and then roughly fuck him until he was begging for a hand on his cock.  

It was fucking _hot_.

And it's not like Dean's embarrassed about how he watches gay porn.  He's made it pretty clear to everyone that he swings both ways.  Because he does, and quite happily at that.  But the awkward part, the thing that's giving his heart all sorts of palpitations, is that maybe for a minute or two there he'd kinda sorta imagined it was Cas and Jimmy going at it.  That Cas had overpowered his brother and was fucking into him like it was his job.  

~~The image was so fucking intense Dean had come in record time.~~

So Dean's a little hesitant to say _anything_  because he just had _five shots_ of whiskey and now he feels like if he doesn't physically bite his lips to restrain himself, he's going to blurt out _all_  of that.  Talk about the two dudes going at each other hard, and not stopping before he mentions he thought of the two brothers _having sex_.  

"Pass."  

"You sure hiding your, ahem, _viewing preferences_ is worth the extra drink?" Jimmy asks, eyebrows wagging suggestively.

He doesn't hesitate before he downs another sip.  He even licks his lips afterward to buy some time.  "Definitely."  And because he's feeling like a cornered animal and needs to deflect attention ASAP, he blurts out, "Cas - truth or dare, buddy?"

Cas blinks a couple times, perhaps surprised that Dean's decided to ask him instead of switching to Jimmy, but answers smoothly enough.  "Well, in consideration of the new amendment of the rules, I suppose I'm going to have to say dare."

Well on his way to being drunk (he might skip tipsy altogether), Dean's mind grasps at straws until it comes up with a somewhat decent suggestion.  "You gotta take off your shirt and go out in the hall.  For the next five minutes, every time someone walks by, you gotta say 'penis' really quietly.  And every step they get closer, you gotta say it a little louder."

"Five minutes seems a bit excessive, Dean."

"Our first dare _and_  first modification."  Jimmy claps his hands gleefully.  "Can I intervene with a suggestion?"  Dean waves at him to go ahead.  "Maybe it should be an either or?  Like, either five minutes of standing there or until ten people go by?  He could get a whole lot of standing around doing nothing, or he could get out of it real quick."

"I accept."

"Dean has to approve it first, Cassie."  

Cas scowls at his brother but when he turns to Dean, he's got these puppy dog eyes that Dean wouldn't have been able to say no to, even if he were sober.  "That's fine, man.  Five minutes or ten people."  

(He ignores the fact that it comes out slurred and more than a little unintelligible.)

The smile he gets from Cas just about fucks him up, only partly because Cas smiling isn't the easiest thing to accomplish.  Mostly it's because it's promptly followed by Cas pulling off his shirt, revealing a beautifully tan chest and the curly hairs leading down into his shorts, and tossing it at Dean.  Dean's reflexes take over when he catches it, thank _god_.  It's mortifying enough that he's _drooling_  over Cas right now.  It'd be a hundred times worse if he'd been rendered incapable of something so basic as catching a fucking shirt too.

While Cas takes his post in the hallway, Dean and Jimmy fight over the peephole.  The rough house a bit to try and get the better position, since realistically only one of them will be able to look out at a time and apparently they don't know how to take turns.  

(And so, okay, it _does_  kinda give Dean an excuse to put his hands on Jimmy.  Pushing him out of the way lets him discreetly feel the muscles under his shirt.   ~~He feels about as strong as Cas looks, _fuck_.~~   Shouldering him to the side gives him great access to his hair and neck, the smell of his shampoo _just_  there.)

( ~~They've gotta stay this close for five whole minutes?  While spying on a shirtless Cas in the hallway?  While Dean is kinda sorta a bit drunk?  Dean is totally fucked.~~ )

Dean could not be more pleased with his choice of dare.  Or brother for said dare, for that matter.  Cas is his usual impassive self (whereas Jimmy would start snickering as soon as someone rounded the corner, ruining the whole thing).  They can only see Cas as he stands maybe four feet away, angled towards their door, and waits patiently.  There's only a subtle shift in his stance that lets them know he's spotted someone.  And yeah, they can't hear the first few times he whispers 'penis', they can _definitely_  hear it by the time the people walk by.  He's practically _yelling_ by the time they briefly appear in view.

It's  _hilarious_.

(Jimmy's biting the inside of his lips to keep from cackling but these breathy little half laughs keep escaping.  It's really fucking distracting, knowing he's breathing Jimmy in with each mouthful of air.)

Most of the girls who walk by try to avoid him by hugging the opposite wall.  A few giggle and whisper, and one of them even comes over to talk to Cas and ask what he's doing.  Cas, however, is committed to his role.  The longer she stays, the louder he gets until she's doubled over laughing and telling him her room number if he wants to stop by later.  Without fail, the guys who pass by laugh and maybe slap him on the shoulder as they walk by.

As soon as the tenth and eleventh people are gone (a couple holding hands - the girl looking skeptically at Cas while the guy high fives him), Cas comes back into the room.  (Dean already misses having Jimmy so close and hates that the first thing Cas does is put his shirt back on.)

"I feel I should get some sort of compensation for having to do that to eleven people instead of the agreed upon ten," he grumps.

"What, you wanted us to go out there and cover one of their ears so they didn't hear you?"  Jimmy pushes his brother into a chair.  "Them's the breaks, bro."

" _Fine_."  He crosses his arms over his chest and glares at his brother.  "Jimmy, I dare you to-"

"Don't I get a choice?"

Dean watches as Cas visibly restrains himself and starts over.  "Jimmy, truth or dare?"

"Dare."

Cas looks like he wants to punch him.  "I dare you to open the window and hit on the first three people that walk by using only the pick-up lines we give you."

"That's not that bad-"

"But if any of them take you up on it, you have to follow through."

Jimmy doesn't dial down his bravado, but does ask, "Define 'follow through', you're not suggesting I actually sleep with them-"

"Obviously not," Cas interrupts.  "But you'll at least have to invite them up and invite them to join us."

(Is it just Dean, or is there so _suggestive_  about the way Cas says 'join us'?)

"Fine, no problem."

They open up the window.  Their dorm rooms are on the second floor and look down on the sidewalk leading to the main entrance.  It's not that late yet, so it shouldn't take too long for three people to walk by.  Dean takes up a spot on one side of Jimmy, mostly out of view of anyone walking by but with enough room that he can peak out.  Cas makes a detour to the twins' mini-fridge and follows suit, throwing Dean a bottle of water and eyeing him menacingly until he drinks half of it.  

Jimmy sneaks a drink of his own, whipping off the excess whiskey with his shirt sleeve, then starts scouting for the first victim.  He nudges them with his feet each time someone stops by.  Dean and Cas google "worst pickup lines" and show each other their phones when they find one they like, stage whispering it to Jimmy who groans but delivers them flawlessly.  

The first guy that walks by just gives Jimmy the finger when he calls down, "Hey beautiful, that shirt is very becoming on you. If I was on you, I'd be coming too."

The second is a girl playing on her cell phone, and she doesn't even acknowledge his presence as he catcalls and then jeers, "Nice legs... what time do they open?"

Neither Dean nor Cas get a look at the third person since they're too busy frantically scrolling to find a good final line.  Giggling, Dean shows Cas a truly terrible one.  His eyes crinkle in what Dean now recognizes as the Cas equivalent of a huge grin.  (And one day, he promises himself, he's going to see Cas grin for real.)

"Excuse me, sir!"  Jimmy waves his hand until he has their attention.  "Sorry for the incovenience, but I'm with the Secret Service.  I see you're walking around with pretty big guns there.  I'm going to need to come up here for a full body cavity search.  National security, you know."

The wrinkles around Cas' eyes intensify about tenfold and Dean can't decide if he wants to keep watching to see that unicorn grin he's been hoping for or howl in laughter.  

Turns out he gets neither, since the line is followed by a brief pause before a stern voice is yelling back, "James Novak, I know you know better than to be drinking and shouting out your window at random people.  Close the fucking window and don't make me come up and do a room inspection!"

Cas and Dean stare at each other in bewilderment, instantly recognizing their RA's voice.

"No no no, sir, you're mistaken.  I'm not this 'James Novak' - sounds like a cool guy though.  I'm with the Secret Service and I really just need to make sure you're not carrying any unauthorized weapons or-"

"Fuck off, Novak."

"Yes, sir!  You have a good night!"  And like that, the window is slammed shut and all three of them are on the ground struggling to breathe.  Jimmy damn near kicks Dean in the head as he collapses on Cas, who halfheartedly tries to push his brother off before succumbing to more near silent laughter.  He's of course far more dignified than either Jimmy or Dean.  Both will get themselves nearly under control then crack up all over again.  

After a while, it works its way out of their systems.  Dean's the first to stand up, wiping tears from his eyes.  He offers a hand to each twin and pulls them up.

"Dude, you've got some serious game," he congratulates.  "If we gave you some decent lines, we'd probably have three more people in here right now."

"They clearly can't handle us or they'd be up here anyway."  He beams at Dean and gives him a once over like he wants to fucking _devour_  him (where the hell did _that_  come from?) before licking his lips and asking, "So Dean... Truth or dare?"

He momentarily plays with the idea of going with truth again, but he's not sure his liver could take it.  He tells Jimmy to hit him with his first dare of the evening and gulps slightly at the mischievous glint in his eye.

( ~~Not because he's nervous about answering, but because he finds it kind of sexy.~~ )

( ~~Wait, what?  No, that's not...  That's not any better...  Fuck.~~ )

"I dare you to streak through the dorm atrium."

"Streak?  Like, naked streak?"

"That is what streaking means, Dean," Cas says gravely.

"That seems like an unfair escalation from yelling out penis and shouting shit out a window."  Is he nervous?  Yeah, maybe a little.  

"Well..."  Jimmy reaches over and finds the whiskey bottle, dangerously close to empty.  "You could always ask for me to modify it if you're not up to it."

Dean snatches the bottle and takes a drink.  

It's Cas who speaks up for him.  "Instead of being naked, how about instead you are to wear underwear."

"No that's too easy."  Jimmy considers for a moment before a solution hits him.  "How about you can wear underwear...  But it has to be your _tightest_  pair of boxer briefs.  The ones you wear under that wrestling outfit."

He's pretty sure his cheeks are an unflattering shade of pink right now.  "How do you...  How do you know about..."

Jimmy shrugs.  "I don't really, but I know you're on the wrestling team and I figured you've gotta have _something_  on under that snug little outfit.  You don't seem like the type to go commando."

It's with great effort that Dean bites back any comments and heads into his room to change.  He's got his dresser open to rummage through it when the twins peak in through the bathroom door.

"No fucking way are you guys watching me change."  And he means it.  Mostly because he doesn't want any awkward boners to explain.

"Fine, but we have to confirm that you actually wear an appropriate garment."

"Cassie's right, can't have you trying to sneak in some boxers or something."

Dean finds his smallest pair (and yeah, they kinda frame his junk nicely, sue him for having noticed) and holds it up for them.  "Good?"  

They both nod.  Cas looks like he's _undressing him_ with his eyes, imagining what he'd look like in nothing but he small red pair of briefs.  And Jimmy... well, he doesn't look like he wants to leave to give him privacy, but Cas pulls him by the sleeve out into the hallway.  

"We're going to scout out seats."

"You're always welcome to grab some more whiskey if you need a little liquid courage to help you out."

And then Dean's alone wondering about his life choices (and if he's imagining the flirty way the twins looked at him before disappearing out the door).  He ignores the whiskey because even with the water Cas forced into him, he's tipsier than he'd like.  And as bad as it is running through the atrium in his damn underwear, the only thing that would make it worse is if he fell on his ass doing it because he was too damn drunk to function like a normal human being.

As he strips down and changes underwear, he plans out his path.  The whole dorm is basically a big square with a courtyard in the center.  He should be able to run right through from one side of the atrium to the other and make a full circuit back around the building to his room.  Not a big deal, really, but he's not worried about the walk to or back.  No, the real issue is the atrium itself.

It's _huge_.  It has a dozen or so tables with chairs, several sofas and a TV, the front desk for signing in guests, and a foosball table.  Not only does it take up almost the whole ground floor of the east side of the building, but the second and third floors look down onto it.  Basically, if you're looking to study on the first three floors of the dorm, you're probably in or around the atrium.  

He silently prays that everyone's out partying since it's Friday.

Dean never did have that much luck.  He sneaks a peak around the corner and sees it's packed.  There's a bunch of kids playing foosball and someone brought an xbox down to play on the TV.  Most of the seats are taken and there's even some card game going on the floor over by where he's going to make his escape.  Perfect.

Cas and Jimmy somehow commandeered one of the smaller tables and are casually talking like they're not about to make their fucking suitemate embarrass himself in front of the whole dorm.  Cas spots him and gets Jimmy's attention.  Jimmy gives him a shit eating grin and a thumbs up; Cas makes a show of looking around the room at all the people there, then makes eye contact with Dean and winking.

Whelp.  Here goes nothing.

He takes a deep breath and then he's going, making a beeline through the tables and around the big sofa to get to the other side.  He only gets a couple feet when Jimmy starts, "OH MY GOD THAT WEIRD GUY'S RUNNING IN HIS PANTIES!"

(Seriously, fuck Jimmy.  These aren't _panties_.  They're just really snug briefs.)

And someone - Cas, he suspects - starts clapping and jeering loudly.  There's silence for a whole heartbeat before everyone's joining in, screaming and cheering and basically total pandemonium.  And because Dean's not shy, not by a long shot, he slows down to wave.  He does a spin and a bow at the end of his run, jumps over the card game and sprints for the nearest stairs.  

He's actually surprised when he gets back to his room and finds that a.) the twins weren't dicks and didn't lock him out and b.) his room is empty.  He steps into his pants and grabs his shirt, heading back to the twins' room.  The shirt's only half-on by the time he steps out of the bathroom, and when he gets it down out of his eyes, he finds the brothers staring at him.

"How'd I do?"

They snap out of their daze and hand Dean a phone.  He takes all of two seconds to realize the fuckers _videotaped_  him.  

"You guys are assholes," he grumbles and throws the phone back at them.  

Jimmy catches it easily and tucks it into his back pocket.  "Careful, is that any way to talk to the guys who have not _yet_  posted this to YouTube?  Get on our bad side and it might just find its way there."

"Are you _blackmailing_  me?"

"Of course not," Cas scoffs.  "We're implying we _could_  blackmail you.  Technically that's different."

"Doesn't feel different," he mumbles as he falls into the only empty chair.  Cas is seated at his desk, his brother on the end of Cas' bed, no doubt so they could watch their video together.  

Ugh, the video.  He doesn't _blame_  them, necessarily, because he'd have done the same thing.  But it the last thing he needs is the snide comments he's going to get from them for the rest of the year.  

This calls for some serious retaliation.  For _both_  of them.  

"Cas.  Truth or dare?"

Cas appraises him for a moment, then gives a faint half-smile, almost a dare in and of itself.  "Dare."

"You just did a dare, drink up."  

"Never took you for a rule stickler," Dean comments as Jimmy brings the bottle over to his brother.  "Thought that'd be more Cas' thing."

"If the rules involve drinking and work against Cas, fuck yeah I'm for rules."  He waits for Cas to take a sip before snatching it and drinking a bit himself.  "Cassie's always been more of a rebel anyway."

Dean's not sure he believes that, but he lets it go.  He was worried he'd have to wait a while to get a chance to get back at them, so he's not about to look a gift horse in the mouth.  "Okay, lemme think of a dare...."  He hmms and makes a show of thinking about it, but he thought of the perfect counter on his way back from the atrium.  "Cas, I dare you to make out with Jimmy."

The brothers sit in stunned silence.  Eventually, Jimmy coughs and asks a shaky, "What?"

Pushing his advantage, Dean goes on.  "Make out.  Which I am going to define as continued lip action for, say, ninety seconds.  Actual kissing, not just leaving your lips closed against each other.  Gotta see some movement in there."

"But you dared _Cas_ -"

He shrugs.  "Okay, so Cas is the only one who's gotta move his lips.  Jimmy, you can just sit back and think of England or whatever."

The brothers look at each other, obviously communicating  _something_.  All Dean gets is Jimmy's apprehension and something he can't quite pinpoint from Cas.  

"I'm game if you are."

Jimmy chews his lip and nods slowly.  

All he can hear is his own blood pumping.  He's not sure if he's drunk on the whiskey anymore or if it's become his fucking excitement that they're going along with this.  Hell, it'll probably be a huge let down, but if it's even _remotely_  as hot as he's imagined, he'll have ~~guilt-inducing~~  spank bank material for months.  Dean grabs his phone and sets a timer, shoots them a smile that's all teeth and nerves.  "Whenever you're ready."  

The twins look at each other for a while before Cas shrugs and leans over to where Jimmy's sitting on the bed.  As soon as their lips hit, Dean starts the timer and holds his breath because _hell yes_.

It starts slow and chaste.  Just the brush of lips a couple times as Cas presses soft kisses to Jimmy's lips.  Jimmy eyes are closed, scrunched tight in an attempt to endure the torture Dean's forced upon him.  He momentarily feels bad, but that thought flies out the window when he sees Cas nibble lightly on Jimmy's bottom limp.  Jimmy whimpers - fucking _whimpers_  - and then starts kissing back.  

Things escalate quickly after that.  With Cas' hand cupping Jimmy's cheek in encouragement, Dean witnesses the exact second Jimmy gives in and kisses back in earnest.  It goes from Cas peppering kisses along Jimmy's lips to the two enthusiastically making out.  Their lips move in tandem as they get more aggressive.  Dean's pretty sure he spots Cas' tongue dipping into Jimmy's mouth and he _definitely_  hears the resulting groan of approval.  

And then it goes up a notch as Cas pulls Jimmy into his lap, arms around his waist to hold him as he wreaks friggin havoc on his brother's mouth.  Jimmy goes along willingly.  Lets his twin manhandle him and have his way with him, moaning appreciatively the whole time.

Dean is speechless.  That's in fact doesn't do it justice.  There are no words, no thoughts, nothing left but the image of Jimmy and Cas going at it in front of him.  His fingers tighten around his phone, the only thing left for him to clutch onto because everything else he's ever thought he knew is crumbling around him.  

Of course, that's about when they start grinding into each other.

The phone slips from Dean's hands, completely forgotten, as he casually shifts and tries to ignore his suddenly massive erection.  This?  This right here?  Hottest fucking thing Dean's ever seen in his goddamned life.  He is never going to get over this moment and the fact that it actually happened and _he got to see it_.  It will forever be ingrained on his retinas.

Seconds or minutes or years later (the timer, still running, could tell him exactly how long, but that would require _looking away_ and fuck looking away), Jimmy looks up and locks eyes with Dean.  Cas doesn't seem to mind the loss of Jimmy's lips, simply moves on to kissing his neck, sucking big angry bruises above his collar and holding him still so he can continue grinding up into him.  

"You enjoying the show?"  Jimmy's lips are kiss swollen and red.  He's fucking _breathless_  as he keeps meeting his brother's slow upward thrusts, keeps tilting his head back to give him more access to his neck.

Dean's mouth has gone dry and he's too stunned to answer.  Words are well beyond his reach at the moment, so he settles for nodding.  Even that's a quick, jerky motion that feels stilted, but it's the best he can do.

"Show me."  He arches his back as Cas pulls his hair ( _pulls his fucking hair_  Jesus Christ) and starts biting along the underside of his jaw.  "Show us how much you like it."

He's not really sure what the protocol is here.  Ignoring the fact that he's watching two twins very roughly dry hump each other, watching two dudes make out...  Well, he's embarrassed about taking his dick out, okay?  This is something that happens in pronos, not in Dean Winchester's honest to god life.  But he can't just sit here and do _nothing_.  Under Jimmy's watchful eye, he starts palming his crotch, spreads his legs and angles his hips so Jimmy an see exactly how hard he is.

Jimmy opens his mouth to say something when he's distracted by Cas' growling.  A hand forcefully pulls him back into a kiss and then there's more tongue and teeth and lips and yeah, Dean's never going to be able to get rid of this image.  This right here?  He's going to have wet dreams about this for the rest of his life.  Never mind how many times he'll actively jerk off this week alone.

But soon Jimmy pulls away completely and slides off of Cas' lap.  Cas grunts in annoyance, makes a move to force him back until he turns enough that he sees Dean languidly stroking himself through his pants.  Then he looks at him hungrily as Jimmy crawls over.  Dean doesn't know where to look.  There's Cas, who clearly wants to push him against a wall and give him the same treatment he gave his brother.  But then there's Jimmy, slipping in between his legs and kneeling in front of him.  

Hands start undoing his pants, and yep, Jimmy's got his full attention.  

He's mesmerized by the sight, from his nimble fingers working his pants down and then running them up the length of his cock, still straining against his red briefs, to his flush cheeks and the eager way his tongue darts out to moisten his lips.  "Dean, can I suck you off?"

There are apparently enough brain cells floating around in his head, since he does manage to get out some sort of response.  He hopes it's a little more articulate (and less desperate) than, "Yes of fucking course, please please _please_."

( ~~It's not.~~ )

And then Jimmy's encouraging him to lift his hips so he can get his clothes completely out of the way.  Dean's legs are numb from the booze and the surrealness of this whole thing, but he shifts as best he can and voila!  Pants and briefs gone.  

"Mmm," Jimmy moans as he licks up the length of Dean's cock.  "Such a fucking gorgeous cock."  And without further preamble he's got Dean's cock in his mouth.  Dean hisses and jumps slightly, lets Jimmy's hands hold him firmly in place while he bobs back and forth.  

Dean has no idea where to look.  Because the image of Jimmy swallowing him down?  Those lips getting stretched by his dick and his eyes watching him and the _sounds_  he makes?  Yeah, that's awesome.  But then he catches sight of Cas, sitting there watching them.  Eyes boring into them greedily as he idly rubs his hand up and down his extremely prominent erection.  Dean's never really been an exhibitionist, but the idea of Cas watching his brother give him head makes his dick twitch in Jimmy's mouth.  

He's drunk right?  He's imagining this, right?  No way this is happening.  

Apparently getting bored of just watching, Cas stands up and walks over.  Dean gulps, no idea what's going to happen, but then Cas' hands are on Jimmy's head.  He holds his brother in place so that Dean's cock is deep in his throat.  Jimmy doesn't struggle, doesn't resist at all as Cas angles his head so they can see Dean's dick pushing against his cheek.  Holding Jimmy firmly by the scalp, Cas' free hand runs along the buldge.  Both Jimmy and Dean groan.  

Dean bucks because he can't help it, and it forces Cas to turn his attention back to him.  Eyes locked, he starts slowly moving Jimmy's head up and down.  He builds up a rhythm then lets go of his hold.  When Jimmy takes over, Cas keeps his hand there to run it through his hair.  

"My brother's very good at giving head, isn't he?"

Wait... what?  

Dean's mind screeches to a halt because _how the fuck is he supposed to read that_?  Is... is Cas speaking from _experience_?  Oh _fuck_ , _fuck_  that's so goddamned _hot_  Dean's brain might explode.  

Somehow in the midst of this internal meltdown, he stutters out, "Yeah, he's good."

He smiles in approval and ducks down to kiss Dean.  Dean barely needs any encouragement to open his mouth and yield to Cas' exploring.  But then exploring changes to something more domineering, Cas staking a claim and forcing him into submission.  He reflexively tries to pull back, to lean away from the hard press of Cas' lips, but Cas' hand grabs the back of his neck and keeps him there.  

Needless to say, he's breathless when Cas abruptly pulls away.  "Are _you_  any good at giving head, Dean?"

Dean very elegantly groans and nods eagerly while he starts pawing at Cas' pants.  Cas tsks at him and steps out of his reach.  He starts to un-do his own pants at a painfully slow pace and pulls them down only enough to free his dick.  Holding the base, he steps forward so that all Dean has to do is lean forward and then he's licking at the precome collecting at the tip.

Once he's done teasing Cas (and he feels he's earned the right to tease him after the way the twins have _taken over_ his dare), he takes him in to the root and stays there until his eyes water.  Dean gets used to the stretch, then starts moving.  At first it happens by accident, him matching Jimmy's pace, but after he notices it's easier to follow.  

Jimmy catches on pretty quick.  He stops moving for a second, waits until Dean looks down, and then he winks and starts again.  Only now, he's changing it up.  No longer satisfied with bobbing up and down, his hand will reach up to tease at his balls.  Or he'll pop off completely, spit dripping down his chin as he licks at the head and tongues the slit.  Or maybe he'll run his nose up the length, tongue following in its wake.  He even rubs his stubbled cheek against Dean's dick once or twice, precome smearing into the coarse hairs.

And Dean?  Dean does it all.  Every time Jimmy cradles his balls, Dean does it too.  He licks and groans and rubs and sucks in all the ways he can feel Jimmy doing it to him.  Whatever Jimmy does to him, he does to Cas.  And whatever Cas does to Dean, Dean does to Jimmy.

So when Cas threads his fingers through Dean's hair and holds him in place to fuck his face for a few strokes, that's what Dean does to Jimmy.  And when he cups Dean's jaw before sliding his hand down to grasp his neck, never exerting pressure but letting him know he _could_ , Dean mirrors the action.  

At some point Cas nudges Jimmy with his foot.  Jimmy follows the silent command and goes back to moving back and forth, forcing Dean to do the same.  "Good boys," he praises.  Then he starts stroking Dean's cheek and brushing stray hairs off his forehead.  "So good for me, Dean.  The next time I'm stretching you open with my cock, it's going to be because I'm drilling you into your bed until you come all over your sheets.  Would you like that?"

Dean moans in answer, and Cas smiles in acknowledgement.  

From between his legs, Jimmy whimpers, his pace faltering for a moment.  "Don't worry."  Cas uses his other hand to pet Jimmy's head, to caress behind his ear and give a quick squeeze to the nape of his neck.  "I'll fuck you into Dean's bed, too.  But you'll have to wait your turn."  Jimmy whimpers again as he relaxes into Cas' touch (but somehow not slowing down as he continues to give Dean the best blowjob of his life).  "Don't worry, I'll let you watch.  Would you like that, Dean?  If Jimmy watched me fuck you into an incoherent mess?"

Answering would require him to stop deep-throating Cas, so he doesn't.  Instead his hands reach around to grab Cas' ass, giving him leverage to enthusiastically fuck himself onto Cas' cock.  

Cas seems to get the message, because he hums in approval.  "Mmmm, good.  Jimmy, unzip your pants and start jerking off."  Jimmy does as he's told, hands fumbling a bit since he refuses to stop or slow down sucking Dean off.  "Can't wait to fuck you both.  I'll fuck Dean first, hard and fast because I bet he'll like being used like that.  Won't you, Dean?"  He waits for Dean's assenting groan.  "Then I'll push Jimmy down, get his face right in your come, and fuck him while he licks up the mess you made.  After he comes, I'll pull out and come all over both of you.  Mark you up so you know who's in charge."

The mental image proves to be too much for Cas.  He worked himself up, loving the prospect of fucking the two of them.  He's barely finished speaking when he's clutching Dean's head, holding him still as he comes so Dean has no choice but to swallows all of it.

As soon as Dean feels the pulses hitting the back of his throat, _he's_  coming with an embarrassingly loud moan.  Jimmy not only swallows but pulls back to lick up every drop that escaped, squeezes the base so that more pools at the tip and gets that too.  Then he's standing over Dean and jacking himself off in earnest.  

Cas slips out of Dean's mouth, patting his head once before taking up position behind Jimmy.  He lines his spent cock up with his twin's ass and thrusts against it a couple times.  His hand winds around to cover Jimmy's, and they work together to get Jimmy off.

"You really gonna fuck us like that, Cassie?"  Jimmy's leaning back into Cas, neck exposed to another assault of sucking, biting kisses.  

"Of course," he growls back.  "I'll take care of both of you, don't worry."

And then it's Jimmy coming all over Dean's softening cock, groaning and rutting back into his brother as he begs and pleads to be fucked.  

Dean's still blissed out, completely limp in his chair, and watches like it's happening to someone else.  Because honestly, that would be easier to believe.  Out of it, he grouses out, "How come I'm the only one that got messy?"

"Hmm, Dean's right.  That's not at all fair."  Cas pushes Jimmy aside and kneels in front of Dean.  Before Dean can ask what he's about to do, he's licking up Jimmy's come.  Dean's poor dick twitches, definitely on board with the proceedings, but unable to get hard again to really enjoy it.  He's too oversensitive, but he loves it too much to pull away.  He bites the inside of his cheek to keep still until Cas is done.

In a daze, Dean's pulled up, one twin on each side of him.  They quickly divest him of his clothing, then each other's, and drag him to the nearest bed.  It's ridiculous, really, because the beds are barely big enough for _one_  six foot tall guy, never mind two.  But _three_?  That's really pushing it.  But somehow they make it work.  

Cas goes first, moving the blankets out of the way so Jimmy can climb in and pull Dean in on top of him.  The twins are cuddled around each other, Dean carefully cradled on top of them.  He's not going to lie, it's a bit lumpy and he'll wake up with a crick in his back, but there's nothing in the world that could convince him to move.  

"You comfortable?"

At some point one of them flicked off the light.  For the life of him, he has no idea which twin asked.  "'m good."

"Good."  He's snuggled closer, a hands coming to rub his back, his shoulders, his hair.  So many hands, everywhere, soothing him until he's drifting off to sleep.  He lays sprawled on top of Jimmy and Cas, who whisper to each other in the dark.  Before he finally passes out, Dean distinctly remembers thinking he could get used to this.  

**Author's Note:**

> Soooo this was supposed to be short. Like, maybe three thousand words??? So not super short, but *much* shorter than it ended up. Whoops??? #sorrynotsorry I think it worked out though. I probably could've skipped a lot of the earlier stuff and gone right to Dean daring Jimmy and Cas to make out, but I wanted a bit more build up. Plus I plan on doing at least two more Dean x Cas X Jimmy fics that kinda follow up on this one, so it felt like a good idea to play around with the characters a bit and get a feel for how I'm going to write them. Jimmy especially since I've never written him before. 
> 
> Misc. Notes:  
> \- Dean is reading Tess of the D'Uebervilles by Thomas Hardy. And as I recall, the story was published on a weekly basis in a newspaper (or something like that). So yes, the author did randomly change some key pieces of information in the story to suit the needs of his plot. Poor guy couldn't go back and change it, either, since the earlier chapters were already published and circulated (kinda like when I fuck up a WIP...). And sometimes he'd put in a few "clues" that things would turn out a certain way or could've gone a different way, but they seem kinda not substantial. Sorry, mini-rant about this book over (if you wanna hear more about my complaints, feel free to hit me up on tumblr... keep in mind, I did enjoy the book, I'm just all too aware of its flaws).
> 
> \- To figure out how many shots they each had to do for the retro-active rule, I actually had to make a little diagram to figure it out lol. So no, I did not arbitrarily assign shots to each of them. 
> 
> \- I also consulted this lovely (i.e. *terrible*) list of bad pickup lines since I wouldn't have been able to come up with any on my own: http://uncyclopedia.wikia.com/wiki/Worst_100_Pick-Up_Lines_of_All_Time


End file.
